Sodium Hydroxide → 3-(2,6-Dichloro-3-nitro-phenyl)-[1,6]naphthyridin-2-ylamine

HRID 270692ノート

反応式

HRID 270692 の反応式
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]#[N:14].[NH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[CH:22]=O.[OH-].[Na+]>CCO.CCOC(C)=O>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13]([NH2:14])=[N:15][C:16]2[C:17]([CH:22]=1)=[CH:18][N:19]=[CH:20][CH:21]=2

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 27610334-AminonicotinaldehydeHCID 598338582-(2,6-Dichloro-3-nitrophenyl)acetonitrile

生成物 1

HCID 598339093-(2,6-Dichloro-3-nitro-phenyl)-[1,6]naphthyridin-2-ylamine収率 23.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2,6-dichloro-3-nitrophenyl-acetonitrile (1.02 g, 4.42 mmol), 4-amino-pyridine-3-carbaldehyde (0.4 g, 3.28 mmol) and NaOH (52 mg, 1.31 mmol) in EtOH (2.0 mL) is heated to 105° C. for 24 hours. The reaction mixture is diluted with EtOAc (50 ml) and washed with saturated K2CO3 and brine. The organic layer is dried, filtered and concentrated to give crude product. Flash silica gel column purification eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (100/6) affords the titled intermediate as a solid (257 mg, 23.4%).

後処理

  1. washwashed with saturated K2CO3 and brine
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product
  6. customFlash silica gel column purification
  7. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (100/6)

出典と根拠

ORDレコード
ord-fe0cbafb60b9493d89f49b0b150ee853
出典データセット
uspto-grants-2008_11
特許番号
US07449582B2

反応ノート

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